Today, we announced that I am the CEO of GiveCorps. Its old news to me since I made the decision 4 months ago, but today was the day we got around to making the announcement. I changed my linkedin a little over a month ago, so for anyone watching, they already knew. However, we needed to make it official, so today we issued a press release.

This last 4 months has reminded me of the summer of 2000. That summer I made a decision that has and will continue to profoundly affect the rest of my life. I knew it was a big decision at the time and I dwelled on it. I labored over that decision for many hours.

In the summer of 2000, I decided to work for a startup called GoPin. It was spinout of Nortel Networks. It was funded by CrossPoint Venture Partners. There were 69 people in Ottawa, Canada working on GoPin. They were planning to use long distance calling cards issued by the Regional Bell Operating Companies as a payment method for digital goods online.

What was I thinking?

I had worked for Talk.com until June 2000. However, I had really stopped working for them back in April. At Talk, I learned a few valuable lessons.

First, do your due diligence. I saw a lot of similarities to what I had been doing at First USA and thought that it would be simple to translate the experience over to long distance. What I didn’t appreciate was that long distance was very different that financial services. Long distance telephony was changing fast and I had no idea. Which led to the next lesson. Don’t work in an industry that is commodity hell. Since there was very limited differentiation between carriers, it became an all out price war within months of my joining Talk.com. I was not prepared for that. Finally, and most importantly, work with people you know and trust. I only interviewed with three people. The CEO, his right hand man and a friendly board member. What I didn’t appreciate was that these people were only one faction of the business. They were brought in to right the ship and take it to the next level, however, there was a whole other side to this business which included a legacy team brought in by the founder. It was an odd mix of this new group that had been with the CEO on several different stints prior and the legacy group. Then there was me. Odd man out!

Every one of these rules I broke and ended up in a job I hated, working with people that I had no connection. That was a bad place to be. However, I have always been good at “failing fast”. If I see that it won’t work, I have no problem cutting and running. In the same vane, I have no problem sticking with something and fighting through obstacles if I believe the mission is worthy and possible. At Talk, it became clear that I made a mistake. However, it would lead to the best career decision I ever made. It only took 7 or 8 years to prove that it was a great career decision.

There were so many great things about that summer. My daughter was born in March of that year. We moved back to the Baltimore area before I had found a new job, so I had a lot of time to spend with my daughter and wife.

I started actively looking for a job and was offered the head of marketing at Advertising.com early that summer. Something didn’t feel right about the job. First, the board member that I interviewed with at Talk.com was on the board of Ad.com too. So, when I started negotiating, they withdrew the offer. I am certain the board member chimed in at that point and I was toast. It’s funny. I knew I didn’t want to work there, but it was the high flying hot startup, so I felt like I should want to work there. It was in my home town. It was an internet advertising company and I was the internet advertiser of the year. A perfect fit, but it wasn’t. I didn’t know the people. I didn’t know the technology. And they had dogs in the office… I am allergic to dogs. My gut was telling me that if I took it, I would be making the same mistakes again. I was glad they pulled out because my rationale side might have over ruled my gut and I might have made another mistake.

Just a month after that offer blew up, I was connected with Gary Marino. We were connected through a common friend. I knew of him but didn’t really know him. However, we had worked at Citibank and First USA at the same time . We shared close relationships with the same colleagues, so even though we hadn’t worked together closely, we had shared language and experience. We were part of the same tribe. We had the same domain expertise. Gary had started working with GoPin as an advisor and CEO in waiting. He was hired by CrossPoint to be parental supervision and domain expert to the Nortel folks who had spun out. He asked me if I wanted to help him out. It felt right. Although I didn’t know him well, we had a common language and common experiences. We were from the same tribe. It felt good and safe. I agreed to work with him on a consultative basis and we would see where it went.

It was a crazy first few months. We quickly realized that phone card payment strategy had all kinds of flaws, but we had 69 people in Ottawa working to make it a reality. The shear mass of them gave their strategy more credibility than it deserved. It was a cluster f#*k! But we did use the time to do some great research on what the consumers and merchants would want in an internet payment option. This research led to Bill Me Later, but it wouldn’t be until 6 months later that Bill Me Later clearly emerged as a strategy. In the meantime, we were trying to figure out how to make an internet payment option out of a long distance phone card. It was painful!

However, we continued to hire. Surround ourselves with our tribe. People we knew and trusted. People with a common language and experience. These were the foundations of what would become a powerful team that built Bill Me Later.

During that summer, it wasn’t so clear that Bill Me Later would emerge out of this morass. In the meantime, I continued to pursue other more stable jobs in Baltimore.

I had always harbored an interest in education. Education changed my life. However, I also saw our public education model as flawed. I felt like I wasted a lot of time until the lightbulb finally went off. I wished that I could have had a better experience earlier. Instead I was trapped in this regimented factory like education model that turned me off rather than lit me up. I always wanted to figure out a better way to educate our young people. Interestingly, Baltimore was home to one of the more successful for profit education companies, sylvan learning centers. I heard of a position opening as the CMO for Sylvan and pursued it aggressively. It was perfect. It was in Baltimore. It would allow me to focus on a passion, education. And it would leverage my functional domain expertise, direct marketing. I couldn’t have scripted it better. This time I did it right. I interviewed with everyone. I even attended company events to get to know the people. But my gut kept nagging at me that it wasn’t right. I didn’t really know the people. I was gun shy to join another tribe. I waited the full two weeks to decide and then finally, I turned the job down. I know I pissed off the President, but it just didn’t feel right.

I remember the hours spent riding my tractor mowing my lawn that summer and mulling over the decision. I struggled with it. I thought I was crazy for even considering doing the GoPin job. The Sylvan job was so clearly a better fit all around.

It was funny, but it felt safer to be with my tribe in a company that really didn’t exist with a product that would never work, then it was to join an established company with a proven product in a senior role working with people I didn’t know and trust. I followed my gut and it worked out. Even joining Talk proved to be a wise decision. If I hadn’t gone to Talk and failed, I wouldn’t have even considered GoPin (which became Bill Me Later). However, the Talk experience taught me what to value in a career decision and serendipitously aligned with the timing of my next opportunity.

All along I was following my gut and it worked out.

So, when I think about this summer with GiveCorps, I remember the anxiety of the summer of 2000 and remind myself to trust my gut, don’t sweat trying to rationalize what your gut is telling you and have faith that it all works out the way it should.

Some people may say this is reckless, but my gut hasn’t let me down this far, so why should I stop trusting it now.

My gut is telling me that we are trying to solve an important problem at GiveCorps. We need to create a more efficient means for Non-profits to leverage the resources of the community to fulfill their missions. Our government is broken and populace are disenfranchised. We need a better way to come together as a society to make our world a better place.

I suspect that I will look back on this decision to join GiveCorps and look back many years from now and be amazed at how this decision has profoundly affected so many lives. That is my goal!

I continue to dare to dream… and I continue to be amazed that my dreams keep coming true!